Synthesis and characterization by 13C-CP-MAS- and high resolution 1H-, 13C-NMR of new ureido sugars, derivatives of methyl 2-amino-2-deoxy-β- d-glucopyranose and dipeptides

Abstract

Dipeptide ethyl and benzyl esters were used as amination agents in reaction with methyl 3,4,6- tri-O- acetyl-2-deoxy-2-(4-nitrophenoxycarbonylamino)-β- d-glucopyranoside(1) . Ten new ureido sugars, derivatives of GlyAla, AlaGly, AlaAla, GlyVal, ValGly, LeuGly, PheGly, GlyPhe, and AlaPhe were obtained. The new ureido sugars were studied by means of 1H- and 13C-NMR spectroscopy in solution, and 13C-CP-MAS-NMR in the solid-state. Dipeptide ethyl and benzyl esters were used as amination agents in reaction with methyl 3,4,6,-tri-O-acetyl-2-deoxy-2-(4-nitrophenoxycarbonylamino)-β- d-glucopyranoside. Ten new ureido sugars, derivatives of GlyAla, AlaGly, AlaAla, GlyVal, ValGly, LeuGly, PheGly, GlyPhe, and AlaPhe were obtained. The new ureido sugars were studied by means of 1H and 13C NMR spectroscopy in solution, and 13C CP MAS NMR in the solid-state.